Whitaker was a left-handed boxer who excelled at the defensive aspect of the sport. He had a stellar amateur boxing career as a lightweight: he won the U.S. Golden Gloves and a silver medal in the World Boxing Championships in 1982, the gold medal at the Pan American Sports Games in 1983, and the gold medal at the Olympic Games in 1984.

Whitaker won his first professional fight, on Nov. 15, 1984, as well as his next 10 fights before getting a title shot. On March 28, 1987, Whitaker won a 12-round decision (a fight whose outcome is determined by judges’ scoring) over American Roger Mayweather to take the North American Boxing Federation (NABF) lightweight title. Although he lost a 12-round decision to José Luis Ramírez of Mexico for the World Boxing Council (WBC) lightweight title on March 12, 1988, Whitaker came back to win the International Boxing Federation (IBF) lightweight title from American Greg Haugen on Feb. 18, 1989, and he added the WBC title by winning a 12-round decision in a rematch with Ramírez on Aug. 20, 1989. Following several successful title defenses, Whitaker knocked out Juan Nazario of Puerto Rico in the first round on Aug. 11, 1990, to win the World Boxing Association (WBA) lightweight title. The following year, he defended his lightweight titles three times, each time winning on a 12-round decision.

Whitaker moved up in weight class to challenge the IBF junior welterweight (also known as super lightweight) champion, Rafael Pineda of Colombia, against whom he won a 12-round decision on July 18, 1992.

Whitaker moved up in weight class again, winning the WBC welterweight title with a 12-round decision over American James (“Buddy”) McGirt on March 6, 1993. On March 4, 1995, Whitaker once again moved up in weight class, winning the WBA junior middleweight (also known as super welterweight) title with a 12-round decision over Julio Cesar Vasquez of Argentina. Whitaker soon abandoned this title in favour of defending his welterweight title, which he finally lost on April 12, 1997, in a 12-round decision to American Oscar de La Hoya. Whitaker next won a 10-round decision over Andrei Pestriaev of Russia on Oct. 17, 1997, but, after Whitaker tested positive for cocaine immediately following the fight, the result was changed to a no contest. Whitaker had one more fight, on Feb. 20, 1999, in which he challenged Puerto Rican Felix Trinidad for his IBF welterweight title, but lost in a 12-round decision. Whitaker finished his professional career with 40 wins (17 by knockouts), 4 losses, 1 draw, and 1 no contest. He was inducted into the International Boxing Hall of Fame in 2007.

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